Episode 019 Bankruptcy Meets The AI Revolution
Jenny Doling didn't wait for AI to be ready for bankruptcy practice — she built it herself, one skill at a time. This episode digs into the analyzer stack she's running for pay stubs, tax returns, bank statements, and Chapter 13 objections, and why she thinks the real win isn't time saved but better legal work. If you're still deciding whether AI belongs in a bankruptcy practice, Jenny's already three steps past that question.
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Show Notes
Episode 019 - Jenny Doling
Most bankruptcy lawyers still don't know what their own firm actually makes each month. Jenny Doling built a revenue dashboard in Claude to find out — and then kept going, building analyzer skills for pay stubs, tax returns, bank statements, and Chapter 13 objections that her staff now runs without her. If a nationally recognized bankruptcy attorney and NACBA's incoming president is running her practice this way, what's the excuse for everyone else?
In this episode:
Jenny Doling's path from paralegal to bankruptcy attorney to NACBA president-elect, and how she got hooked on consumer bankruptcy work back in 2004
The scale of the current bankruptcy surge — commercial and individual filings both up sharply since 2022 — and what firms without systems risk
Why Jenny moved her practice from ChatGPT to Claude, and how she uses Claude skills, projects, and Cowork day to day
The analyzer stack she built: pay stub analyzer, document renamer, bill analyzer, tax return analyzer, and bank statement analyzer
Her Chapter 13 Opposition Builder skill — loaded with trustee objections, Collier on Bankruptcy material, docket reports, and key case law
Confidentiality practices: a closed Claude Team environment, a written office AI policy, and PII lockdowns before staff touch any tool
Why Jenny separates time saved from work-product elevation, and argues the second is the real benefit of AI
Client-facing AI disclosures in her fee agreements, and why she avoids Zoom's built-in AI transcription specifically
A frank take on legal tech vendor Glade versus incumbents like Clio, and why responsiveness matters more than market share
This week's Season 2 build step: organizing the firm knowledge assets identified last week, tiered by Flintstones, Simpsons, and Jetsons lawyers
We also discuss:
Case law and citation practices for Chapter 13 objections, including Hamilton v. Lanning
Recording practices — why "team record" doesn't mean "team Zoom record"
AI transcription and notetaking tools, including Whisper, Granola, and wearable recorders
NACBA's upcoming AI-focused conference programming in Orlando and Maui
A Practice Signal segment on a solo PI lawyer's shrinking case volume and how Jenny would advise him to diversify
Key Takeaway
Jenny Doling isn't impressive because she uses AI. She's impressive because she treats her analyzer skills as infrastructure — quality control built in, confidentiality locked down before staff ever touch a tool, and her name still on every pleading that goes out the door. That's the difference between dabbling and running a practice.
This one's for the Simpsons lawyer wondering how far a solo or small firm can actually take this. It gives Flintstones lawyers permission to start small, and it gives Jetsons lawyers something sharper to aim for — the difference between an old-school Jetsons practice and what Jenny calls "AI Jetsons."
Mentioned in This Episode
NACBA (National Association of Consumer Bankruptcy Attorneys)
Claude (skills, projects, artifacts, Cowork)
ChatGPT
Best Case Desktop
Jubilee
Next Chapter
SharePoint / OneDrive
Clio
Glade
